解決

described_class.perform_later rescue nil

RSpec.describe MyJob, type: :job do
  include ActiveJob::TestHelper

  context 'when `MyError` is raised' do
    before do
      allow_any_instance_of(described_class).to receive(:perform).and_raise(MyError.new)
    end

    it 'makes 4 attempts' do
      assert_performed_jobs 4 do
        described_class.perform_later rescue nil
      end
    end

    it 'does something in the `retry_on` block' do
      expect(Something).to receive(:something)

      perform_enqueued_jobs do
        described_class.perform_later rescue nil
      end
    end
  end
end
perform_nowでは再実施は発生しないよう

疑問

rescue nil を付与しなくても動きそう?

ruby on rails - How to properly test ActiveJob’s retry_on method with rspec? - Stack Overflow